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2026-03-27

2026-03-28
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Chicago holiday rentals

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100 results

  • Charming 5 Bedrooms 2 Bathrooms

    8027 South Kimbark Avenue, Chicago, United States (To the map)

    To the hotel

    Book Now
  • Immaculate Brand New Penthouse Chicago

    From US$ 799

    1630 West Warren Boulevard, Chicago, United States (To the map)

    To the hotel

    price for 1 night
    Book Now From US$ 799
  • Modern 4 Bedroom Condo In Lakeview

    West Barry Avenue 2100, Chicago, United States (To the map)

    To the hotel

    Book Now
  • 8Br Kids Room, Game Room, Gym Andtheater

    4038 N Central Ave, Chicago, Il 60634, Usa, Chicago, United States (To the map)

    To the hotel

    Book Now
  • Top 1 Rated 4Br Lincoln Park House - King Bed

    210 W St Paul Ave, Chicago, Il 60614, Usa, Chicago, United States (To the map)

    To the hotel

    Book Now
  • The Retreat - Hot Tub, Theater, Game Room, Fire Pit, Bar, Sleeps 14

    4505 North Harding Avenue, Chicago, United States (To the map)

    To the hotel

    Book Now
  • Hello Again, Chicago!

    1856 West Huron Street, Chicago, United States (To the map)

    To the hotel

    Book Now
  • Pet-Friendly With Pool Table Walk To Wrigley Field

    From US$ 1249

    1045 W Dakin St Unit 1, Chicago, United States (To the map)

    To the hotel

    price for 1 night
    Book Now From US$ 1249
  • 2 Newly Built Luxury Condos With Private Roofdeck

    From US$ 2399

    811 N Sedgwick St, Chicago, United States (To the map)

    To the hotel

    price for 1 night
    Book Now From US$ 2399
  • Beautifully Remodeled Flat Downtown #3N

    From US$ 239

    858 North Orleans Street #3N, Chicago, United States (To the map)

    To the hotel

    price for 1 night
    Book Now From US$ 239
  • Luxury Gold Coast Penthouse With Deck & Views

    22 East Elm Street, Chicago, United States (To the map)

    To the hotel

    Book Now
  • Spacious 3-Bed West Loop Townhouse, 1 Car Garage

    920 W Van Buren St, Chicago, United States (To the map)

    To the hotel

    Book Now
  • Ultra Modern Luxury - New Construction 4 Bedrooms

    5039 North Winthrop Avenue, Chicago, United States (To the map)

    To the hotel

    Book Now
  • Chicago 1Br, Stylish Stay With Workspace

    3114 W Waveland Ave Unit 1A, Chicago, Il 60618, Usa, Chicago, United States (To the map)

    To the hotel

    Book Now
  • Amazing Wicker Park Penthouse With Skyline Views

    1549 North Milwaukee Avenue #4, Chicago, United States (To the map)

    To the hotel

    Book Now
  • White Sox Best House

    From US$ 162

    3801 South Calumet Avenue, Chicago, United States (To the map)

    To the hotel

    price for 1 night
    Book Now From US$ 162
  • Chicago Home With Spacious Yard 14 Mi To Dtwn

    From US$ 112

    Chicago, United States (To the map)

    The 2-bedroom Chicago Home With Spacious Yard 14 Mi To Dtwn is around 12 minutes' walk from A. Philip Randolph Pullman Porter Museum, while Indoor Water Park is around 3 km away. This property is…

    To the hotel

    price for 1 night
    Book Now From US$ 112
  • Huge Projector And Designated Workspace, Near Wrigley

    From US$ 992

    3116 W Waveland Ave, Unit 2B, Chicago, Il 60618, Usa, Chicago, United States (To the map)

    To the hotel

    price for 1 night
    Book Now From US$ 992
  • New Construction Building In River North

    From US$ 1119

    811 N Sedgwick St, Chicago, United States (To the map)

    To the hotel

    price for 1 night
    Book Now From US$ 1119
  • Envitae Hotel 4Br Modern Sleek Apartment

    853 West Blackhawk Street, Chicago, United States (To the map)

    To the hotel

    Book Now